Sending the Wrong Message

All right, you did it again. You obviously didn’t learn your lesson from the last time you pulled that stunt. It’s all over, bucko. You’re toast. You know perfectly well what you did. You went off and sent that email to the wrong person, said the wrong thing to the right person, or did something perfectly foolish with email. Your face is red. I can see that right from my side of the monitor. You close down your email program, shut off the computer, and skulk away, wondering if your reputation has been damaged beyond repair. All the disclaimers in the world aren’t going to get you out of this one. You’re on email probation now.

Almost everyone has distributed a personal message to the wrong person at one time or another. Those who haven’t are merely waiting for their turn to come. It’s practically inevitable. If you haven’t already done so, you will. I have.

Ross Kodner calls it the “oh-no-second,” that flick of a lapse between your brain and your mouse that sends the unstoppable. You call it disaster.

A quick hit on “send,” and before your finger levitates a single millimeter from the mouse, you realize that a personal messages is now zooming through space to the screens of unintended eyes across the world. There’s no postmaster from whom the missent missive can be retrieved. You can only dream that the recipient will think that an evil someone spoofed your address.

PRIVILEGED – ATTORNEY CLIENT CONFIDENTIAL began one lawyer’s email to a client, outlining strategies not meant for the eyes and ears of others. But a slip of a click led the message to distribution to a mailing list of over a thousand lawyers. The errant lawyer immediately caught her mistake, and sent forth a second message, bearing the subject line “Emergency! Do Not Open, and Delete if You Do,” confessing her sin of sending confidential mail to the list, asking recipients to delete the mail, not to forward it, and to treat it otherwise with the respect usually reserved for toxic waste. And then she followed up with a plea to the list manager, asking that the missent missive be wiped from the archives and offering to pay all expenses associated with its removal. The lawyer did all that could reasonably be done to control the damage on a Sunday morning.

“Judge Juan Fulano is big fat idiot and his breath stinks” your message read. You intended to send it to Lisa Loopner, but it went off to Lisa Loopinski instead, because you relied upon the autocomplete feature to dredge up all of the Lisas in your address book, letting it finish the address after you’d typed in L-i.

No autocomplete for you. You used it, and it abused you. Give it up. All the careful keyboarding in the world won’t save you from its dangers. Jim Calloway, Oklahoma State Bar Association Practice Management Advisor, describes how to disable autocomplete in Outlook at Jim Calloway’s Law Practice Tips Blog. In Eudora, it’s as simple as Tools | Options | Auto-completion.

Eudora also has the BossWatch feature, which warns users before sending email to selected addresses.

Email encryption is widely available and easier to use than ever. So, why aren’t more lawyers taking the time to encrypt email? Or does the problem lie with the recipient who can’t figure out how to use the Captain Magic decoder ring?

It’s possible to prevent those potentially humiliating situations.

• Let the mail season at least a few minutes before sending. Disable Immediate Send, sending off email after enough time has elapsed for the ink to dry. A few minutes isn’t going to make a great difference in the grander scheme of things. Even a couple of hours.
• Check, check and double-check what goes out. Oh, but lawyers are always in such a rush.
• Slow down.
• Edit messages carefully, paying proper attention to grammar and punctuation, and verify the recipient’s email address more than with a cursory glance.
• If you still can’t trust yourself, use a completely different email address for mailing list mail than you use for important client mail.
• Hire an armed guard to monitor your email habits.

When your fingers fly off in the wrong direction, it’s not the end of the world. Recall the message, hoping against hope. Apologize and mean it. Take that pledge to be careful the next time seriously. Realize that everyone makes mistakes.

On the other hand, there’s always Paraguay. Change your name, undergo some serious plastic surgery, enter the Witness Protection Program, and move to the unnamed city populated by bus drivers who’ve fled the scene of horrifying accidents in third world countries.

jennifer j. rose, editor-in-chief of GP|Solo, receives her email at jjrose@jjrose.com in Morelia, Michoacán, Mexico. This column originally appeared in Technology eReport, published by the American Bar Association General Practice, Solo and Small Firm Division.

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One comment on “Sending the Wrong Message”

Your article really brings back (bad) memories. I’m forever second-guessing what I just wrote, so I added a rule to Outlook that delays delivery for one minute. That way the message sits in the Outbox for a while before leaving for good, allowing me to double-click and edit it and avoid embarrassment.